N1-substituted-5-fluoro-2-oxopyrimidinone-1(2H)-carboxamide derivatives

ABSTRACT

This present disclosure is related to the field of N1-substituted-5-fluoro-2-oxopyrimidinone-1-(2H)-carboxamides and their derivatives and to the use of these compounds as fungicides.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. application Ser. No.12/851,331, filed Aug. 5, 2010, which claims priority to U.S.Provisional Application No. 61/232,245, filed on Aug. 7, 2009, thedisclosures of which are expressly incorporated by reference herein.

BACKGROUND AND SUMMARY OF THE INVENTION

Fungicides are compounds, of natural or synthetic origin, which act toprotect and/or cure plants against damage caused by agriculturallyrelevant fungi. Generally, no single fungicide is useful in allsituations. Consequently, research is ongoing to produce fungicides thatmay have better performance, are easier to use, and cost less.

The present disclosure relates toN1-substituted-5-fluoro-2-oxopyrimidinone-1(2H)-carboxamide compoundsand their use as fungicides. The compounds of the present disclosure mayoffer protection against ascomycetes, basidiomycetes, deuteromycetes andoomycetes.

One embodiment of the present disclosure may include compounds ofFormula I:

wherein R¹ is:

-   -   H;    -   C₁-C₆ alkyl optionally substituted with 1-3 R⁴;    -   C₁-C₆ alkenyl optionally substituted with 1-3 R⁴;    -   C₃-C₆ alkynyl optionally substituted with 1-3 R⁴;    -   phenyl, or benzyl wherein each of the phenyl or the benzyl may        be optionally substituted with 1-3 R⁵, or with a 5- or        6-membered saturated or unsaturated ring system, or with a 5-6        fused ring system, or with a 6-6 fused ring system each        containing 1-3 heteroatoms wherein each ring may be optionally        substituted with 1-3 R⁵, biphenyl or naphthyl optionally        substituted with 1-3 R⁵;    -   —(CHR⁶)_(m)OR⁷;    -   —C(═O)R⁸;    -   —C(═S)R⁸;    -   —C(═O)OR⁸;    -   —C(═S)OR⁸;    -   —(CHR⁶)_(m)N(R⁹)R¹⁰;    -   —C(═O)N(R⁹)R¹⁰; or    -   —C(═S)N(R⁹)R¹⁰;        wherein m is an integer 1-3;        R² is H or C₁-C₆ alkyl optionally substituted with R⁴;        alternatively R¹ and R² may be taken together to form        ═CR¹¹N(R¹²)R¹³;        R³ is —C(═O)N(R⁹)R¹⁰ or —C(═S)N(R⁹)R¹⁰;        R⁴ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio,        halothio, amino, C₁-C₃ alkylamino, C₂-C₆ alkoxycarbonyl, C₂-C₆        alkylcarbonyl, C₂-C₆ alkylaminocarbonyl, hydroxyl, or C₃-C₆        trialkylsilyl;        R⁵ is independently halogen, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆        alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ haloalkylthio,        halothio, amino, C₁-C₆ alkylamino, C₂-C₆ dialkylamino, C₂-C₆        alkoxycarbonyl, or C₂-C₆ alkylcarbonyl, nitro, hydroxyl, or        cyano;        R⁶ is H, C₁-C₆ alkyl, C₁-C₆ alkoxy, benzyl or phenyl wherein        each of the benzyl or phenyl may be optionally substituted with        1-3 R⁵;        R⁷ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆ alkylcarbonyl, phenyl, or        benzyl wherein each of the phenyl, or the benzyl may be        optionally substituted with 1-3 R⁵, or with a 5- or 6-membered        saturated or unsaturated ring system, or with a 5-6 fused ring        system, or with a 6-6 fused ring system each containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵, biphenyl or naphthyl optionally substituted with 1-3 R⁵;        R⁸ is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆        haloalkyl, C₁-C₆ alkoxyalkyl, phenyl or benzyl wherein each of        the phenyl or the benzyl may be optionally substituted with 1-3        R⁵, or with a 5- or 6-membered saturated or unsaturated ring        system, or with a 5-6 fused ring system, or with a 6-6 fused        ring system each containing 1-3 heteroatoms wherein each ring        may be optionally substituted with 1-3 R⁵, biphenyl or naphthyl        optionally substituted with 1-3 R⁵;        R⁹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl, C₁-C₆        alkylalkoxycarbonyl, C₂-C₆ alkylcarbonyl, —(CH₂)_(m)SCH₃ phenyl        or benzyl wherein each of the phenyl or the benzyl may be        optionally substituted with 1-3 R⁵, or with a 5- or 6-membered        saturated or unsaturated ring system, or with a 5-6 fused ring        system, or with a 6-6 fused ring system each containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵, biphenyl or naphthyl optionally substituted with 1-3 R⁵        R¹⁰ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆        alkylcarbonyl, benzyl, wherein the benzyl may be optionally        substituted with 1-3 R⁵;        alternatively R⁹ and R¹⁰ may be taken together to form a 5- or        6-membered saturated or unsaturated ring containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵;        R¹¹ is H or C₁-C₄ alkyl;        R¹² is H, cyano, hydroxyl, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆,        alkylcarbonyl, phenyl or benzyl wherein each of the phenyl or        the benzyl may be optionally substituted with 1-3 R⁵; or with a        5- or 6-membered saturated or unsaturated ring system, or with a        5-6 fused ring system, or with a 6-6 fused ring system each        containing 1-3 heteroatoms wherein each ring may be optionally        substituted with 1-3 R⁵, biphenyl or naphthyl optionally        substituted with 1-3 R⁵;        alternatively R¹¹ and R¹² may be taken together to form a 5- or        6-membered saturated or unsaturated ring containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵;        R¹³ is H, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆, alkylcarbonyl,        phenyl or benzyl wherein each of the phenyl or the benzyl may be        optionally substituted with 1-3 R⁵; and        alternatively R¹² and R¹³ may be taken together to form a 5- or        6-membered saturated or unsaturated ring containing 1-3        heteroatoms wherein each ring may be optionally substituted with        1-3 R⁵.

Another embodiment of the present disclosure may include a fungicidalcomposition for the control or prevention of fungal attack comprisingthe compounds described below and a phytologically acceptable carriermaterial.

Yet another embodiment of the present disclosure may include a methodfor the control or prevention of fungal attack on a plant, the methodincluding the steps of applying a fungicidally effective amount of oneor more of the compounds described below to at least one of the fungus,the plant, an area adjacent to the plant, and the seed adapted toproduce the plant.

The term “alkyl” refers to a branched, unbranched, or cyclic carbonchain, including methyl, ethyl, propyl, butyl, isopropyl, isobutyl,tertiary butyl, pentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl and the like.

The term “alkenyl” refers to a branched, unbranched or cyclic carbonchain containing one or more double bonds including ethenyl, propenyl,butenyl, isopropenyl, isobutenyl, cyclohexenyl, and the like.

The term “alkynyl” refers to a branched or unbranched carbon chaincontaining one or more triple bonds including propynyl, butynyl and thelike.

As used throughout this specification, the term ‘R’ refers to the groupconsisting of C₂₋₈ alkyl, C₃₋₈ alkenyl or C₃₋₈ alkynyl, unless statedotherwise.

The term “alkoxy” refers to an —OR substituent.

The term “alkoxycarbonyl” refers to a —C(O)—OR substituent.

The term “alkylcarbonyl” refers to a —C(O)—R substituent.

The term “alkylsulfonyl” refers to an —SO₂—R substituent.

The term “haloalkylsulfonyl” refers to an —SO₂—R substituent where R isfully or partially substituted with Cl, F, I, or Br or any combinationthereof.

The term “alkylthio” refers to an —S—R substituent.

The term “halothio” refers to a sulfur substituted with three or five Fsubstituents.

The term “haloalkylthio” refers to an alkylthio, which is substitutedwith Cl, F, I, or Br or any combination thereof.

The term “alkylaminocarbonyl” refers to a —C(O)—N(H)—R substituent.

The term “dialkylaminocarbonyl” refers to a —C(O)—NR₂ substituent.

The term “alkylalkoxycarbonyl” refers to a —(CH₂)_(m)C(O)OR substituent.

The term “alkylcycloalkylamino” refers to a cycloalkylamino substituentthat is substituted with an alkyl group.

The term “trialkylsilyl” refers to —SiR₃.

The term “cyano” refers to a —C≡N substituent.

The term “hydroxyl” refers to an —OH substituent.

The term “amino” refers to a —NH₂ substituent.

The term “alkylamino” refers to a —N(H)—R substituent.

The term “dialkylamino” refers to a —NR₂ substituent.

The term “alkoxyalkoxy” refers to —O(CH₂)_(n)O(CH₂)_(m)CH₃ where n is1-3 and m is 0-2.

The term “alkoxyalkyl” refers to an alkoxy substitution on an alkyl.

The term “haloalkoxyalkyl” refers to an alkoxy substitution on an alkylwhich is fully or partially substituted with Cl, F, Br, or I, or anycombination thereof.

The term “hydroxyalkyl” refers to an alkyl which is substituted with ahydroxyl group.

The term “haloalkoxy” refers to an —OR—X substituent, wherein X is Cl,F, Br, or I, or any combination thereof.

The term “haloalkyl” refers to an alkyl, which is substituted with Cl,F, I, or Br or any combination thereof.

The term “haloalkenyl” refers to an alkenyl, which is substituted withCl, F, I, or Br or any combination thereof.

The term “haloalkynyl” refers to an alkynyl which is substituted withCl, F, I, or Br or any combination thereof.

The term “halogen” or “halo” refers to one or more halogen atoms,defined as F, Cl, Br, and I.

The term “hydroxycarbonyl” refers to a —C(O)—OH substituent.

The term “nitro” refers to a —NO₂ substituent.

Throughout the disclosure, reference to the compounds of Formula I isread as also including optical isomers and salts of Formula I, andhydrates thereof. Specifically, when Formula I contains a branched chainalkyl group, it is understood that such compounds include opticalisomers and racemates thereof. Exemplary salts include: hydrochloride,hydrobromide, hydroiodide, and the like. Additionally, the compounds ofFormula I may include tautomeric forms.

Certain compounds disclosed in this document can exist as one or moreisomers. It will be appreciated by those skilled in the art that oneisomer may be more active than the others. The structures disclosed inthe present disclosure are drawn in only one geometric form for clarity,but are intended to represent all geometric and tautomeric forms of themolecule.

It is also understood by those skilled in the art that additionalsubstitution is allowable, unless otherwise noted, as long as the rulesof chemical bonding and strain energy are satisfied and the productstill exhibits fungicidal activity.

Another embodiment of the present disclosure is a use of a compound ofFormula I, for protection of a plant against attack by a phytopathogenicorganism or the treatment of a plant infested by a phytopathogenicorganism, comprising the application of a compound of Formula I, or acomposition comprising the compound to soil, a plant, a part of a plant,foliage, and/or seeds.

Additionally, another embodiment of the present disclosure is acomposition useful for protecting a plant against attack by aphytopathogenic organism and/or treatment of a plant infested by aphytopathogenic organism comprising a compound of Formula I and aphytologically acceptable carrier material.

Additional features and advantages of the present invention will becomeapparent to those skilled in the art upon consideration of the followingdetailed description of the illustrative embodiments exemplifying thebest mode of carrying out the invention as presently perceived.

DETAILED DESCRIPTION OF THE PRESENT DISCLOSURE

The compounds of the present disclosure may be applied by any of avariety of known techniques, either as the compounds or as formulationscomprising the compounds. For example, the compounds may be applied tothe roots, seeds or foliage of plants for the control of various fungi,without damaging the commercial value of the plants. The materials maybe applied in the form of any of the generally used formulation types,for example, as solutions, dusts, wettable powders, flowableconcentrates, or emulsifiable concentrates.

Preferably, the compounds of the present disclosure are applied in theform of a formulation, comprising one or more of the compounds ofFormula I with a phytologically acceptable carrier. Concentratedformulations may be dispersed in water, or other liquids, forapplication, or formulations may be dust-like or granular, which maythen be applied without further treatment. The formulations can beprepared according to procedures that are conventional in theagricultural chemical art.

The present disclosure contemplates all vehicles by which one or more ofthe compounds may be formulated for delivery and use as a fungicide.Typically, formulations are applied as aqueous suspensions or emulsions.Such suspensions or emulsions may be produced from water-soluble, watersuspendible, or emulsifiable formulations which are solids, usuallyknown as wettable powders; or liquids, usually known as emulsifiableconcentrates, aqueous suspensions, or suspension concentrates. As willbe readily appreciated, any material to which these compounds may beadded may be used, provided it yields the desired utility withoutsignificant interference with the activity of these compounds asantifungal agents.

Wettable powders, which may be compacted to form water dispersiblegranules, comprise an intimate mixture of one or more of the compoundsof Formula I, an inert carrier and surfactants. The concentration of thecompound in the wettable powder may be from about 10 percent to about 90percent by weight based on the total weight of the wettable powder, morepreferably about 25 weight percent to about 75 weight percent. In thepreparation of wettable powder formulations, the compounds may becompounded with any finely divided solid, such as prophyllite, talc,chalk, gypsum, Fuller's earth, bentonite, attapulgite, starch, casein,gluten, montmorillonite clays, diatomaceous earths, purified silicatesor the like. In such operations, the finely divided carrier andsurfactants are typically blended with the compound(s) and milled.

Emulsifiable concentrates of the compounds of Formula I may comprise aconvenient concentration, such as from about 10 weight percent to about50 weight percent of the compound, in a suitable liquid, based on thetotal weight of the concentrate. The compounds may be dissolved in aninert carrier, which is either a water-miscible solvent or a mixture ofwater-immiscible organic solvents, and emulsifiers. The concentrates maybe diluted with water and oil to form spray mixtures in the form ofoil-in-water emulsions. Useful organic solvents include aromatics,especially the high-boiling naphthalenic and olefinic portions ofpetroleum such as heavy aromatic naphtha. Other organic solvents mayalso be used, for example, terpenic solvents, including rosinderivatives, aliphatic ketones, such as cyclohexanone, and complexalcohols, such as 2-ethoxyethanol.

Emulsifiers which may be advantageously employed herein may be readilydetermined by those skilled in the art and include various nonionic,anionic, cationic and amphoteric emulsifiers, or a blend of two or moreemulsifiers. Examples of nonionic emulsifiers useful in preparing theemulsifiable concentrates include the polyalkylene glycol ethers andcondensation products of alkyl and aryl phenols, aliphatic alcohols,aliphatic amines or fatty acids with ethylene oxide, propylene oxidessuch as the ethoxylated alkyl phenols and carboxylic esters solubilizedwith the polyol or polyoxyalkylene. Cationic emulsifiers includequaternary ammonium compounds and fatty amine salts. Anionic emulsifiersinclude the oil-soluble salts (e.g., calcium) of alkylaryl sulfonicacids, oil-soluble salts or sulfated polyglycol ethers and appropriatesalts of phosphated polyglycol ether.

Representative organic liquids which may be employed in preparing theemulsifiable concentrates of the compounds of the present invention arethe aromatic liquids such as xylene, propyl benzene fractions; or mixednaphthalene fractions, mineral oils, substituted aromatic organicliquids such as dioctyl phthalate; kerosene; dialkyl amides of variousfatty acids, particularly the dimethyl amides of fatty glycols andglycol derivatives such as the n-butyl ether, ethyl ether or methylether of diethylene glycol, and the methyl ether of triethylene glycoland the like. Mixtures of two or more organic liquids may also beemployed in the preparation of the emulsifiable concentrate. Organicliquids include xylene, and propyl benzene fractions, with xylene beingmost preferred in some cases. Surface-active dispersing agents aretypically employed in liquid formulations and in an amount of from 0.1to 20 percent by weight based on the combined weight of the dispersingagent with one or more of the compounds. The formulations can alsocontain other compatible additives, for example, plant growth regulatorsand other biologically active compounds used in agriculture.

Aqueous suspensions comprise suspensions of one or more water-insolublecompounds of Formula I, dispersed in an aqueous vehicle at aconcentration in the range from about 5 to about 50 weight percent,based on the total weight of the aqueous suspension. Suspensions areprepared by finely grinding one or more of the compounds, and vigorouslymixing the ground material into a vehicle comprised of water andsurfactants chosen from the same types discussed above. Othercomponents, such as inorganic salts and synthetic or natural gums, mayalso be added to increase the density and viscosity of the aqueousvehicle. It is often most effective to grind and mix at the same time bypreparing the aqueous mixture and homogenizing it in an implement suchas a sand mill, ball mill, or piston-type homogenizer.

Aqueous emulsions comprise emulsions of one or more water-insolublepesticidally active ingredients emulsified in an aqueous vehicle at aconcentration typically in the range from about 5 to about 50 weightpercent, based on the total weight of the aqueous emulsion. If thepesticidally active ingredient is a solid it must be dissolved in asuitable water-immiscible solvent prior to the preparation of theaqueous emulsion. Emulsions are prepared by emulsifying the liquidpesticidally active ingredient or water-immiscible solution thereof intoan aqueous medium typically with inclusion of surfactants that aid inthe formation and stabilization of the emulsion as described above. Thisis often accomplished with the aid of vigorous mixing provided by highshear mixers or homogenizers.

The compounds of Formula I can also be applied as granular formulations,which are particularly useful for applications to the soil. Granularformulations generally contain from about 0.5 to about 10 weightpercent, based on the total weight of the granular formulation of thecompound(s), dispersed in an inert carrier which consists entirely or inlarge part of coarsely divided inert material such as attapulgite,bentonite, diatomite, clay or a similar inexpensive substance. Suchformulations are usually prepared by dissolving the compounds in asuitable solvent and applying it to a granular carrier which has beenpreformed to the appropriate particle size, in the range of from about0.5 to about 3 mm. A suitable solvent is a solvent in which the compoundis substantially or completely soluble. Such formulations may also beprepared by making a dough or paste of the carrier and the compound andsolvent, and crushing and drying to obtain the desired granularparticle.

Dusts containing the compounds of Formula I may be prepared byintimately mixing one or more of the compounds in powdered form with asuitable dusty agricultural carrier, such as, for example, kaolin clay,ground volcanic rock, and the like. Dusts can suitably contain fromabout 1 to about 10 weight percent of the compounds, based on the totalweight of the dust.

The formulations may additionally contain adjuvant surfactants toenhance deposition, wetting and penetration of the compounds onto thetarget crop and organism. These adjuvant surfactants may optionally beemployed as a component of the formulation or as a tank mix. The amountof adjuvant surfactant will typically vary from 0.01 to 1.0 percent byvolume, based on a spray-volume of water, preferably 0.05 to 0.5 volumepercent. Suitable adjuvant surfactants include, but are not limited toethoxylated nonyl phenols, ethoxylated synthetic or natural alcohols,salts of the esters or sulfosuccinic acids, ethoxylated organosilicones,ethoxylated fatty amines and blends of surfactants with mineral orvegetable oils. The formulations may also include oil-in-water emulsionssuch as those disclosed in U.S. patent application Ser. No. 11/495,228,the disclosure of which is expressly incorporated by reference herein.

The formulations may optionally include combinations that contain otherpesticidal compounds. Such additional pesticidal compounds may befungicides, insecticides, herbicides, nematocides, miticides,arthropodicides, bactericides or combinations thereof that arecompatible with the compounds of the present invention in the mediumselected for application, and not antagonistic to the activity of thepresent compounds. Accordingly, in such embodiments, the otherpesticidal compound is employed as a supplemental toxicant for the sameor for a different pesticidal use. The compounds of Formula I and thepesticidal compound in the combination can generally be present in aweight ratio of from 1:100 to 100:1.

The compounds of the present disclosure may also be combined with otherfungicides to form fungicidal mixtures and synergistic mixtures thereof.The fungicidal compounds of the present disclosure are often applied inconjunction with one or more other fungicides to control a wider varietyof undesirable diseases. When used in conjunction with otherfungicide(s), the presently claimed compounds may be formulated with theother fungicide(s), tank mixed with the other fungicide(s) or appliedsequentially with the other fungicide(s). Such other fungicides mayinclude 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol,8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin,Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis,Bacillus subtilis strain ZAT713, benalaxyl, benomyl,benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt,bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen,blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole,bupirimate, calcium polysulfide, captafol, captan, carbendazim,carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil,chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate,copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprousoxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil,dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate),dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran,diethofencarb, difenoconazole, difenzoquat ion, diflumetorim,dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton,dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine,dodine free base, edifenphos, enestrobin, epoxiconazole, ethaboxam,ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil,fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph,fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole,flusilazole, flusulfamide, flutianil, flutolanil, flutriafol,fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium,fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates,GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalilsulfate, imibenconazole, iminoctadine, iminoctadine triacetate,iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone,iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam,isotianil, kasugamycin, kasugamycin hydrochloride hydrate,kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb,mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuricoxide, mercurous chloride, metalaxyl, mefenoxam, metalaxyl-M, metam,metam-ammonium, metam-potassium, metam-sodium, metconazole,methasulfocarb, methyl iodide, methyl isothiocyanate, metiram,metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam,nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fattyacids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate,oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen,pentachlorophenol, pentachlorophenyl laurate, penthiopyrad,phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin,polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassiumhydroxyquinoline sulfate, probenazole, prochloraz, procymidone,propamocarb, propamocarb hydrochloride, propiconazole, propineb,proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin,pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox,pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen,quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam,simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate, sodiumpentachlorophenoxide, spiroxamine, sulfur, SYP-Z071, SYP-Z048, tar oils,tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole,thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl,tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole,tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram,zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp.,Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp.,(RS)—N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide,1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate,1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane,2-(2-heptadecyl-2-imidazolin-1-yl)ethanol,2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide,2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride,2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine,4-(2-nitroprop-1-enyl)phenyl thiocyanateme, ampropylfos, anilazine,azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox,bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl,bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmiumcalcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone,chloraniformethan, chlorfenazole, chlorquinox, climbazole, cyclafuramid,cypendazole, cyprofuram, decafentin, dichlone, dichlozoline,diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon,dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole,etem, ethirim, fenaminosulf, fenapanil, fenitropan, 5-fluorocytosine andprofungicides thereof, fluotrimazole, furcarbanil, furconazole,furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin,halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos,isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam,methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride,myclozolin, N-3,5-dichlorophenyl-succinimide,N-3-nitrophenylitaconimide, natamycin,N-ethylmercurio-4-toluenesulfonanilide, nickelbis(dimethyldithiocarbamate), OCH, phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, picolinamideUK-2A and derivatives thereof, prothiocarb; prothiocarb hydrochloride,pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol;quinacetol sulfate, quinazamid, quinconazole, rabenzazole,salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen,thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos,triarimol, triazbutil, trichlamide, urbacid, and zarilamide, and anycombinations thereof.

Additionally, the compounds of the present invention may be combinedwith other pesticides, including insecticides, nematocides, miticides,arthropodicides, bactericides or combinations thereof that arecompatible with the compounds of the present invention in the mediumselected for application, and not antagonistic to the activity of thepresent compounds to form pesticidal mixtures and synergistic mixturesthereof. The fungicidal compounds of the present disclosure may beapplied in conjunction with one or more other pesticides to control awider variety of undesirable pests. When used in conjunction with otherpesticides, the presently claimed compounds may be formulated with theother pesticide(s), tank mixed with the other pesticide(s) or appliedsequentially with the other pesticide(s). Typical insecticides include,but are not limited to: antibiotic insecticides such as allosamidin andthuringiensin; macrocyclic lactone insecticides such as spinosad andspinetoram; avermectin insecticides such as abamectin, doramectin,emamectin, eprinomectin, ivermectin and selamectin; milbemycininsecticides such as lepimectin, milbemectin, milbemycin oxime andmoxidectin; arsenical insecticides such as calcium arsenate, copperacetoarsenite, copper arsenate, lead arsenate, potassium arsenite andsodium arsenite; botanical insecticides such as anabasine, azadirachtin,d-limonene, nicotine, pyrethrins, cinerins, cinerin I, cinerin II,jasmolin I, jasmolin II, pyrethrin I, pyrethrin II, quassia, rotenone,ryania and sabadilla; carbamate insecticides such as bendiocarb andcarbaryl; benzofuranyl methylcarbamate insecticides such as benfuracarb,carbofuran, carbosulfan, decarbofuran and furathiocarb;dimethylcarbamate insecticides dimitan, dimetilan, hyquincarb andpirimicarb; oxime carbamate insecticides such as alanycarb, aldicarb,aldoxycarb, butocarboxim, butoxycarboxim, methomyl, nitrilacarb, oxamyl,tazimcarb, thiocarboxime, thiodicarb and thiofanox; phenylmethylcarbamate insecticides such as allyxycarb, aminocarb, bufencarb,butacarb, carbanolate, cloethocarb, dicresyl, dioxacarb, EMPC,ethiofencarb, fenethacarb, fenobucarb, isoprocarb, methiocarb,metolcarb, mexacarbate, promacyl, promecarb, propoxur, trimethacarb, XMCand xylylcarb; dessicant insecticides such as boric acid, diatomaceousearth and silica gel; diamide insecticides such as chlorantraniliprole,cyantraniliprole and flubendiamide; dinitrophenol insecticides such asdinex, dinoprop, dinosam and DNOC; fluorine insecticides such as bariumhexafluorosilicate, cryolite, sodium fluoride, sodium hexafluorosilicateand sulfluramid; formamidine insecticides such as amitraz,chlordimeform, formetanate and formparanate; fumigant insecticides suchas acrylonitrile, carbon disulfide, carbon tetrachloride, chloroform,chloropicrin, para-dichlorobenzene, 1,2-dichloropropane, ethyl formate,ethylene dibromide, ethylene dichloride, ethylene oxide, hydrogencyanide, iodomethane, methyl bromide, methylchloroform, methylenechloride, naphthalene, phosphine, sulfuryl fluoride andtetrachloroethane; inorganic insecticides such as borax, calciumpolysulfide, copper oleate, mercurous chloride, potassium thiocyanateand sodium thiocyanate; chitin synthesis inhibitors such asbistrifluoron, buprofezin, chlorfluazuron, cyromazine, diflubenzuron,flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron,noviflumuron, penfluoron, teflubenzuron and triflumuron; juvenilehormone mimics such as epofenonane, fenoxycarb, hydroprene, kinoprene,methoprene, pyriproxyfen and triprene; juvenile hormones such asjuvenile hormone I, juvenile hormone II and juvenile hormone III;moulting hormone agonists such as chromafenozide, halofenozide,methoxyfenozide and tebufenozide; moulting hormones such as α-ecdysoneand ecdysterone; moulting inhibitors such as diofenolan; precocenes suchas precocene I, precocene II and precocene III; unclassified insectgrowth regulators such as dicyclanil; nereistoxin analogue insecticidessuch as bensultap, cartap, thiocyclam and thiosultap; nicotinoidinsecticides such as flonicamid; nitroguanidine insecticides such asclothianidin, dinotefuran, imidacloprid and thiamethoxam; nitromethyleneinsecticides such as nitenpyram and nithiazine; pyridylmethyl-amineinsecticides such as acetamiprid, imidacloprid, nitenpyram andthiacloprid; organochlorine insecticides such as bromo-DDT, camphechlor,DDT, pp′-DDT, ethyl-DDD, HCH, gamma-HCH, lindane, methoxychlor,pentachlorophenol and TDE; cyclodiene insecticides such as aldrin,bromocyclen, chlorbicyclen, chlordane, chlordecone, dieldrin, dilor,endosulfan, alpha-endosulfan, endrin, HEOD, heptachlor, HHDN, isobenzan,isodrin, kelevan and mirex; organophosphate insecticides such asbromfenvinfos, chlorfenvinphos, crotoxyphos, dichlorvos, dicrotophos,dimethylvinphos, fospirate, heptenophos, methocrotophos, mevinphos,monocrotophos, naled, naftalofos, phosphamidon, propaphos, TEPP andtetrachlorvinphos; organothiophosphate insecticides such asdioxabenzofos, fosmethilan and phenthoate; aliphatic organothiophosphateinsecticides such as acethion, amiton, cadusafos, chlorethoxyfos,chlormephos, demephion, demephion-O, demephion-S, demeton, demeton-O,demeton-S, demeton-methyl, demeton-O-methyl, demeton-S-methyl,demeton-S-methylsulphon, disulfoton, ethion, ethoprophos, IPSP,isothioate, malathion, methacrifos, oxydemeton-methyl, oxydeprofos,oxydisulfoton, phorate, sulfotep, terbufos and thiometon; aliphaticamide organothiophosphate insecticides such as amidithion, cyanthoate,dimethoate, ethoate-methyl, formothion, mecarbam, omethoate, prothoate,sophamide and vamidothion; oxime organothiophosphate insecticides suchas chlorphoxim, phoxim and phoxim-methyl; heterocyclicorganothiophosphate insecticides such as azamethiphos, coumaphos,coumithoate, dioxathion, endothion, menazon, morphothion, phosalone,pyraclofos, pyridaphenthion and quinothion; benzothiopyranorganothiophosphate insecticides such as dithicrofos and thicrofos;benzotriazine organothiophosphate insecticides such as azinphos-ethyland azinphos-methyl; isoindole organothiophosphate insecticides such asdialifos and phosmet; isoxazole organothiophosphate insecticides such asisoxathion and zolaprofos; pyrazolopyrimidine organothiophosphateinsecticides such as chlorprazophos and pyrazophos; pyridineorganothiophosphate insecticides such as chlorpyrifos andchlorpyrifos-methyl; pyrimidine organothiophosphate insecticides such asbutathiofos, diazinon, etrimfos, lirimfos, pirimiphos-ethyl,pirimiphos-methyl, primidophos, pyrimitate and tebupirimfos; quinoxalineorganothiophosphate insecticides such as quinalphos andquinalphos-methyl; thiadiazole organothiophosphate insecticides such asathidathion, lythidathion, methidathion and prothidathion; triazoleorganothiophosphate insecticides such as isazofos and triazophos; phenylorganothiophosphate insecticides such as azothoate, bromophos,bromophos-ethyl, carbophenothion, chlorthiophos, cyanophos, cythioate,dicapthon, dichlofenthion, etaphos, famphur, fenchlorphos, fenitrothionfensulfothion, fenthion, fenthion-ethyl, heterophos, jodfenphos,mesulfenfos, parathion, parathion-methyl, phenkapton, phosnichlor,profenofos, prothiofos, sulprofos, temephos, trichlormetaphos-3 andtrifenofos; phosphonate insecticides such as butonate and trichlorfon;phosphonothioate insecticides such as mecarphon; phenylethylphosphonothioate insecticides such as fonofos and trichloronat;phenyl phenylphosphonothioate insecticides such as cyanofenphos, EPN andleptophos; phosphoramidate insecticides such as crufomate, fenamiphos,fosthietan, mephosfolan, phosfolan and pirimetaphos;phosphoramidothioate insecticides such as acephate, isocarbophos,isofenphos, isofenphos-methyl, methamidophos and propetamphos;phosphorodiamide insecticides such as dimefox, mazidox, mipafox andschradan; oxadiazine insecticides such as indoxacarb; oxadiazolineinsecticides such as metoxadiazone; phthalimide insecticides such asdialifos, phosmet and tetramethrin; pyrazole insecticides such astebufenpyrad, tolefenpyrad; phenylpyrazole insecticides such asacetoprole, ethiprole, fipronil, pyrafluprole, pyriprole andvaniliprole; pyrethroid ester insecticides such as acrinathrin,allethrin, bioallethrin, barthrin, bifenthrin, bioethanomethrin,cyclethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin,gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin,beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin,deltamethrin, dimefluthrin, dimethrin, empenthrin, fenfluthrin,fenpirithrin, fenpropathrin, fenvalerate, esfenvalerate, flucythrinate,fluvalinate, tau-fluvalinate, furethrin, imiprothrin, meperfluthrin,metofluthrin, permethrin, biopermethrin, transpermethrin, phenothrin,prallethrin, profluthrin, pyresmethrin, resmethrin, bioresmethrin,cismethrin, tefluthrin, terallethrin, tetramethrin, tetramethylfluthrin,tralomethrin and transfluthrin; pyrethroid ether insecticides such asetofenprox, flufenprox, halfenprox, protrifenbute and silafluofen;pyrimidinamine insecticides such as flufenerim and pyrimidifen; pyrroleinsecticides such as chlorfenapyr; tetramic acid insecticides such asspirotetramat; tetronic acid insecticides such as spiromesifen; thioureainsecticides such as diafenthiuron; urea insecticides such as flucofuronand sulcofuron; and unclassified insecticides such as closantel, coppernaphthenate, crotamiton, EXD, fenazaflor, fenoxacrim, hydramethylnon,isoprothiolane, malonoben, metaflumizone, nifluridide, plifenate,pyridaben, pyridalyl, pyrifluquinazon, rafoxanide, sulfoxaflor,triarathene and triazamate, and any combinations thereof.

Additionally, the compounds of the present invention may be combinedwith herbicides that are compatible with the compounds of the presentinvention in the medium selected for application, and not antagonisticto the activity of the present compounds to form pesticidal mixtures andsynergistic mixtures thereof. The fungicidal compounds of the presentdisclosure may be applied in conjunction with one or more herbicides tocontrol a wide variety of undesirable plants. When used in conjunctionwith herbicides, the presently claimed compounds may be formulated withthe herbicide(s), tank mixed with the herbicide(s) or appliedsequentially with the herbicide(s). Typical herbicides include, but arenot limited to: amide herbicides such as allidochlor, beflubutamid,benzadox, benzipram, bromobutide, cafenstrole, CDEA, cyprazole,dimethenamid, dimethenamid-P, diphenamid, epronaz, etnipromid,fentrazamide, flupoxam, fomesafen, halosafen, isocarbamid, isoxaben,napropamide, naptalam, pethoxamid, propyzamide, quinonamid and tebutam;anilide herbicides such as chloranocryl, cisanilide, clomeprop,cypromid, diflufenican, etobenzanid, fenasulam, flufenacet, flufenican,mefenacet, mefluidide, metamifop, monalide, naproanilide, pentanochlor,picolinafen and propanil; arylalanine herbicides such as benzoylprop,flampropand flamprop-M; chloroacetanilide herbicides such as acetochlor,alachlor, butachlor, butenachlor, delachlor, diethatyl, dimethachlor,metazachlor, metolachlor, S-metolachlor, pretilachlor, propachlor,propisochlor, prynachlor, terbuchlor, thenylchlor and xylachlor;sulfonanilide herbicides such as benzofluor, perfluidone, pyrimisulfanand profluazol; sulfonamide herbicides such as asulam, carbasulam,fenasulam and oryzalin; thioamide herbicides such as chlorthiamid;antibiotic herbicides such as bilanafos; benzoic acid herbicides such aschloramben, dicamba, 2,3,6-TBA and tricamba; pyrimidinyloxybenzoic acidherbicides such as bispyribac and pyriminobac; pyrimidinylthiobenzoicacid herbicides such as pyrithiobac; phthalic acid herbicides such aschlorthal; picolinic acid herbicides such as aminopyralid, clopyralidand picloram; quinolinecarboxylic acid herbicides such as quinclorac andquinmerac; arsenical herbicides such as cacodylic acid, CMA, DSMA,hexaflurate, MAA, MAMA, MSMA, potassium arsenite and sodium arsenite;benzoylcyclohexanedione herbicides such as mesotrione, sulcotrione,tefuryltrione and tembotrione; benzofuranyl alkylsulfonate herbicidessuch as benfuresate and ethofumesate; benzothiazole herbicides such asbenzazolin; carbamate herbicides such as asulam, carboxazolechlorprocarb, dichlormate, fenasulam, karbutilate and terbucarb;carbanilate herbicides such as barban, BCPC, carbasulam, carbetamide,CEPC, chlorbufam, chlorpropham, CPPC, desmedipham, phenisopham,phenmedipham, phenmedipham-ethyl, propham and swep; cyclohexene oximeherbicides such as alloxydim, butroxydim, clethodim, cloproxydim,cycloxydim, profoxydim, sethoxydim, tepraloxydim and tralkoxydim;cyclopropylisoxazole herbicides such as isoxachlortole and isoxaflutole;dicarboximide herbicides such as cinidon-ethyl, flumezin, flumiclorac,flumioxazin and flumipropyn; dinitroaniline herbicides such asbenfluralin, butralin, dinitramine, ethalfluralin, fluchloralin,isopropalin, methalpropalin, nitralin, oryzalin, pendimethalin,prodiamine, profluralin and trifluralin; dinitrophenol herbicides suchas dinofenate, dinoprop, dinosam, dinoseb, dinoterb, DNOC, etinofen andmedinoterb; diphenyl ether herbicides such as ethoxyfen; nitrophenylether herbicides such as acifluorfen, aclonifen, bifenox,chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycofen,fluoronitrofen, fomesafen, furyloxyfen, halosafen, lactofen, nitrofen,nitrofluorfen and oxyfluorfen; dithiocarbamate herbicides such asdazomet and metam; halogenated aliphatic herbicides such as alorac,chloropon, dalapon, flupropanate, hexachloroacetone, iodomethane, methylbromide, monochloroacetic acid, SMA and TCA; imidazolinone herbicidessuch as imazamethabenz, imazamox, imazapic, imazapyr, imazaquin andimazethapyr; inorganic herbicides such as ammonium sulfamate, borax,calcium chlorate, copper sulfate, ferrous sulfate, potassium azide,potassium cyanate, sodium azide, sodium chlorate and sulfuric acid;nitrile herbicides such as bromobonil, bromoxynil, chloroxynil,dichlobenil, iodobonil, ioxynil and pyraclonil; organophosphorusherbicides such as amiprofos-methyl, anilofos, bensulide, bilanafos,butamifos, 2,4-DEP, DMPA, EBEP, fosamine, glufosinate, glufosinate-P,glyphosate and piperophos; phenoxy herbicides such as bromofenoxim,clomeprop, 2,4-DEB, 2,4-DEP, difenopenten, disul, erbon, etnipromid,fenteracol and trifopsime; oxadiazoline herbicides such as methazole,oxadiargyl, oxadiazon; oxazole herbicides such as fenoxasulfone;phenoxyacetic herbicides such as 4-CPA, 2,4-D, 3,4-DA, MCPA,MCPA-thioethyl and 2,4,5-T; phenoxybutyric herbicides such as 4-CPB,2,4-DB, 3,4-DB, MCPB and 2,4,5-TB; phenoxypropionic herbicides such ascloprop, 4-CPP, dichlorprop, dichlorprop-P, 3,4-DP, fenoprop, mecopropand mecoprop-P; aryloxyphenoxypropionic herbicides such as chlorazifop,clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenoxaprop-P,fenthiaprop, fluazifop, fluazifop-P, haloxyfop, haloxyfop-P,isoxapyrifop, metamifop, propaquizafop, quizalofop, quizalofop-P andtrifop; phenylenediamine herbicides such as dinitramine and prodiamine;pyrazole herbicides such as pyroxasulfone; benzoylpyrazole herbicidessuch as benzofenap, pyrasulfotole, pyrazolynate, pyrazoxyfen, andtopramezone; phenylpyrazole herbicides such as fluazolate, nipyraclofen,pioxaden and pyraflufen; pyridazine herbicides such as credazine,pyridafol and pyridate; pyridazinone herbicides such as brompyrazon,chloridazon, dimidazon, flufenpyr, metflurazon, norflurazon, oxapyrazonand pydanon; pyridine herbicides such as aminopyralid, cliodinate,clopyralid, dithiopyr, fluoroxypyr, haloxydine, picloram, picolinafen,pyriclor, thiazopyr and triclopyr; pyrimidinediamine herbicides such asiprymidam and tioclorim; quaternary ammonium herbicides such ascyperquat, diethamquat, difenzoquat, diquat, morfamquat and paraquat;thiocarbamate herbicides such as butylate, cycloate, di-allate, EPTC,esprocarb, ethiolate, isopolinate, methiobencarb, molinate, orbencarb,pebulate, prosulfocarb, pyributicarb, sulfallate, thiobencarb,tiocarbazil, tri-allate and vernolate; thiocarbonate herbicides such asdimexano, EXD and proxan; thiourea herbicides such as methiuron;triazine herbicides such as dipropetryn, indaziflam, triaziflam andtrihydroxytriazine; chlorotriazine herbicides such as atrazine,chlorazine, cyanazine, cyprazine, eglinazine, ipazine, mesoprazine,procyazine, proglinazine, propazine, sebuthylazine, simazine,terbuthylazine and trietazine; methoxytriazine herbicides such asatraton, methometon, prometon, secbumeton, simeton and terbumeton;methylthiotriazine herbicides such as ametryn, aziprotryne, cyanatryn,desmetryn, dimethametryn, methoprotryne, prometryn, simetryn andterbutryn; triazinone herbicides such as ametridione, amibuzin,hexazinone, isomethiozin, metamitron and metribuzin; triazole herbicidessuch as amitrole, cafenstrole, epronaz and flupoxam; triazoloneherbicides such as amicarbazone, bencarbazone, carfentrazone,flucarbazone, ipfencarbazone, propoxycarbazone, sulfentrazone andthiencarbazone-methyl; triazolopyrimidine herbicides such ascloransulam, diclosulam, florasulam, flumetsulam, metosulam, penoxsulamand pyroxsulam; uracil herbicides such as benzfendizone, bromacil,butafenacil, flupropacil, isocil, lenacil, saflufenacil and terbacil;urea herbicides such as benzthiazuron, cumyluron, cycluron,dichloralurea, diflufenzopyr, isonoruron, isouron, methabenzthiazuron,monisouron and noruron; phenylurea herbicides such as anisuron, buturon,chlorbromuron, chloreturon, chlorotoluron, chloroxuron, daimuron,difenoxuron, dimefuron, diuron, fenuron, fluometuron, fluothiuron,isoproturon, linuron, methiuron, methyldymron, metobenzuron,metobromuron, metoxuron, monolinuron, monuron, neburon, parafluoron,phenobenzuron, siduron, tetrafluoron and thidiazuron;pyrimidinylsulfonylurea herbicides such as amidosulfuron, azimsulfuron,bensulfuron, chlorimuron, cyclosulfamuron, ethoxysulfuron,flazasulfuron, flucetosulfuron, flupyrsulfuron, foramsulfuron,halosulfuron, imazosulfuron, mesosulfuron, metazosulfuron, nicosulfuron,orthosulfamuron, oxasulfuron, primisulfuron, propyrisulfuron,pyrazosulfuron, rimsulfuron, sulfometuron, sulfosulfuron andtrifloxysulfuron; triazinylsulfonylurea herbicides such aschlorsulfuron, cinosulfuron, ethametsulfuron, iodosulfuron, metsulfuron,prosulfuron, thifensulfuron, triasulfuron, tribenuron, triflusulfuronand tritosulfuron; thiadiazolylurea herbicides such as buthiuron,ethidimuron, tebuthiuron, thiazafluoron and thidiazuron; andunclassified herbicides such as acrolein, allyl alcohol,aminocyclopyrachlor, azafenidin, bentazone, benzobicyclon,bicyclopyrone, buthidazole, calcium cyanamide, cambendichlor,chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, cinmethylin,clomazone, CPMF, cresol, cyanamide, ortho-dichlorobenzene, dimepiperate,endothal, fluoromidine, fluridone, fluorochloridone, flurtamone,fluthiacet, indanofan, methyl isothiocyanate, OCH, oxaziclomefone,pentachlorophenol, pentoxazone, phenylmercury acetate, prosulfalin,pyribenzoxim, pyriftalid, quinoclamine, rhodethanil, sulglycapin,thidiazimin, tridiphane, trimeturon, tripropindan and tritac.

Another embodiment of the present disclosure is a method for the controlor prevention of fungal attack. This method comprises applying to thesoil, plant, roots, foliage, seed or locus of the fungus, or to a locusin which the infestation is to be prevented (for example applying tocereal or grape plants), a fungicidally effective amount of one or moreof the compounds of Formula I. The compounds are suitable for treatmentof various plants at fungicidal levels, while exhibiting lowphytotoxicity. The compounds may be useful both in a protectant and/oran eradicant fashion.

The compounds have been found to have significant fungicidal effectparticularly for agricultural use. Many of the compounds areparticularly effective for use with agricultural crops and horticulturalplants. Additional benefits may include, but are not limited to,improving the health of a plant; improving the yield of a plant (e.g.increased biomass and/or increased content of valuable ingredients);improving the vigor of a plant (e.g. improved plant growth and/orgreener leaves); improving the quality of a plant (e.g. improved contentor composition of certain ingredients); and improving the tolerance toabiotic and/or biotic stress of the plant.

It will be understood by those in the art that the efficacy of thecompound for the foregoing fungi establishes the general utility of thecompounds as fungicides.

The compounds have broad ranges of activity against fungal pathogens.Exemplary pathogens may include, but are not limited to, wheat leafblotch (Septoria tritici, also known as Mycosphaerella graminicola),apple scab (Venturia inaequalis), and Cercospora leaf spots of sugarbeets (Cercospora beticola), peanut leaf spots (Cercospora arachidicolaand Cercosporidium personatum) and other crops, and black sigatoka ofbananas (Mycosphaerella fujiensis). The exact amount of the activematerial to be applied is dependent not only on the specific activematerial being applied, but also on the particular action desired, thefungal species to be controlled, and the stage of growth thereof, aswell as the part of the plant or other product to be contacted with thecompound. Thus, all the compounds, and formulations containing the same,may not be equally effective at similar concentrations or against thesame fungal species.

The compounds are effective in use with plants in a disease-inhibitingand phytologically acceptable amount. The term “disease-inhibiting andphytologically acceptable amount” refers to an amount of a compound thatkills or inhibits the plant disease for which control is desired, but isnot significantly toxic to the plant. This amount will generally be fromabout 0.1 to about 1000 ppm (parts per million), with 1 to 500 ppm beingpreferred. The exact amount of a compound required varies with thefungal disease to be controlled, the type of formulation employed, themethod of application, the particular plant species, climate conditions,and the like. A suitable application rate is typically in the range fromabout 0.10 to about 4 pounds/acre (about 0.01 to 0.45 grams per squaremeter, g/m²).

Any range or desired value given herein may be extended or alteredwithout losing the effects sought, as is apparent to the skilled personfor an understanding of the teachings herein.

The compounds of Formula I may be made using well-known chemicalprocedures. Intermediates not specifically mentioned in this disclosureare either commercially available, may be made by routes disclosed inthe chemical literature, or may be readily synthesized from commercialstarting materials utilizing standard procedures.

The following examples are presented to illustrate the various aspectsof the compounds of the present disclosure and should not be construedas limitations to the claims.

Example 1 Preparation of4-(dimethylamino-methyleneamino)-5-fluoro-2-oxo-2H-pyrimidine-1-carboxylicacid propylamide (1)

To a 7 milliliter (mL) screw-cap vial were added dichloromethane(CH₂Cl₂; 5 milliliters (mL)),N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (200milligrams (mg), 1.09 millimoles (mmol)), and propyl isocyanate (94 mg,1.10 mmol). The mixture was shaken at room temperature for 16 hours (h).After evaporation and recrystallization of the crude product from CH₂Cl₂and heptane, the title compound was isolated as a white solid (274 mg,94%): mp 266-268° C.; ¹H NMR (300 MHz, CDCl₃) δ 10.42 (br s, 1H), 8.84(s, 1H), 8.46 (d, J=6.6 Hz, 1H), 3.39-3.30 (m, 2H), 3.25 (s, 6H),1.70-1.57 (m, 2H), 0.97 (t, J=7.4 Hz, 3H); ESIMS m/z 270 ([M+H]⁺).

Compound 2 was prepared as in Example 1.

Example 2 Preparation of(E)-N-benzyl-4-((dimethylamino)methyleneamino)-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide(3)

To a suspension ofN′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (0.25 g,1.35 mmol) in CH₂Cl₂ (5 mL) was added benzyl isocyanate (0.187 mL, 1.49mmol) forming a solution that was stirred at room temperature overnight.The mixture was diluted with CH₂Cl₂ (100 mL) and was washed with brine(2×50 mL). The combined aqueous layers were extracted with CH₂Cl₂ (2×25mL). The organic extracts were dried over sodium sulfate (Na₂SO₄),filtered and concentrated. The residue was purified by normal phasechromatography (gradient, methanol/CH₂Cl₂) and then by reverse phasechromatography (gradient, acetonitrile (CH₃CN) in water (H₂O)). Theresulting solution was concentrated under reduced pressure forming aprecipitate. The mixture was extracted with CH₂Cl₂ (4×100 mL), dried(Na₂SO₄), filtered and concentrated to yield(E)-N-benzyl-4-((dimethylamino)methyleneamino)-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide(0.268 g, 62%) as a white solid: mp 147-150° C.; ¹H NMR (300 MHz, CDCl₃)δ 10.83 (t, J=4.94 Hz, 1H), 8.81 (s, 1H), 8.44 (d, J=6.59 Hz, 1H),7.32-7.22 (m, 5H), 4.56 (d, J=5.93 Hz, 2H), 3.21 (s, 3H), 3.20 (s, 3H);ESIMS m/z 318.2 ([M+H]⁺).

Example 3 Preparation of4-amino-5-fluoro-2-oxo-N-pentylpyrimidine-1(2H)-carboxamide (4)

To a suspension ofN′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (0.25 g,1.35 mmol) in CH₂Cl₂ (5 mL) was added pentyl isocyanate (0.194 mL, 1.49mmol) forming a solution that was stirred at room temperature for 3 h.The solvent was removed to give a solid residue that was purified byreverse phase chromatography (gradient, CH₃CN/H₂O) to yield4-amino-5-fluoro-2-oxo-N-pentylpyrimidine-1(2H)-carboxamide (0.022 g,6%) as a white solid: mp 289-292° C.; ¹H NMR (300 MHz, DMSO-d₆) δ 10.27(t, J=5.49 Hz, 1H), 8.43 (s, 1H), 8.32 (d, J=7.58 Hz, 1H), 8.19 (s, 1H),3.24 (q, J=6.99 Hz, 2H), 1.51-1.46 (m, 2H), 1.3-1.21 (m, 4H), 0.85 (t,J=6.59 Hz, 3H); ESIMS m/z 241.2 ([M−H]⁻).

Example 4 Preparation of4-amino-N-cyclopentyl-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide (5)

To a suspension ofN′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (0.25 g,1.35 mmol) in CH₂Cl₂ (5 mL) was added cyclopentyl isocyanate (0.168 mL,1.49 mmol) forming a solution that was stirred at room temperature for 3h. The solvent was removed to give a solid residue that was purified byreverse phase chromatography (gradient, CH₃CN/H₂O) to yield4-amino-N-cyclopentyl-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide (0.018g, 5%) as a white solid: mp 294-297° C.; ¹H NMR (300 MHz, DMSO-d₆) δ10.37 (d, J=6.59 Hz, 1H), 8.43 (s, 1H), 8.32 (d, J=7.58 Hz, 1H), 8.18(s, 1H), 4.03 (sext, J=6.92 Hz, 1H), 1.94-1.85 (m, 2H), 1.68-1.39 (m,6H); ESIMS m/z 239.1 ([M−H]⁻)

Example 5 Preparation of4-amino-5-fluoro-2-oxo-N-phenylpyrimidine-1(2H)-carboxamide (6)

To a suspension of 4-amino-5-fluoro-pyrimidin-2-ol* (0.25 g, 1.94 mmol)in dry N,N-dimethylformamide (DMF; 5 mL) was added phenyl isocyanate(0.231 mL, 2.13 mmol), and the mixture was stirred at room temperaturefor 1 h. The suspension was suction filtered, and washed with diethylether (Et₂O; 3×10 mL). The resulting solid was air-dried overnight toyield 4-amino-5-fluoro-2-oxo-N-phenylpyrimidine-1(2H)-carboxamide (0.32g, 66%) as a white solid: mp 275-277° C. dec; ¹H NMR (300 MHz, DMSO-d₆)δ 12.81 (s, 1H), 8.63 (s, 1H), 8.43 (d, J=7.25 Hz, 1H), 8.35 (s, 1H),7.55 (d, J=7.58 Hz, 2H), 7.37 (t, J=7.58 Hz, 2H), 7.13 (t, J=7.25 Hz,1H); ESIMS m/z 247.1 ([M−H]⁻).4-Amino-5-fluoropyrimidin-2-ol can be purchased commercially.

Compounds 7-13 in Table I were synthesized as in Example 5.

Example 6 Preparation of4-amino-N-(3-chlorophenyl)-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide(14)

Using the procedure of Example 5 but using tetrahydrofuran (THF) insteadof DMF as solvent, 4-amino-5-fluoro-pyrimidin-2-ol (0.25 g, 1.94 mmol)and 3-chlorophenyl isocyanate (0.260 mL, 2.13 mmol) were reacted toyield4-amino-N-(3-chlorophenyl)-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide(0.45 g, 82%) as a white solid: mp 250-252° C.; ¹H NMR (300 MHz,DMSO-d₆) δ 12.82 (s, 1H), 8.65 (s, 1H), 8.43 (d, J=7.3 Hz, 1H), 8.35 (s,1H), 7.29-7.20 (m, 2H), 7.06 (d, J=7.4 Hz, 1H), 6.71 (d, J=8.4 Hz, 1H);ESIMS m/z 280.9 ([M−H]⁻).

Compounds 15-27 in Table I were synthesized as in Example 6.

Example 7 Preparation of5-fluoro-4-(2-fluorobenzylamino)-2-oxo-N-phenylpyrimidine-1(2H)-carboxamide(28)

A 25 mL screw-top vial was charged with5-fluoro-4-(2-fluorobenzylamino)pyrimidin-2-ol (74.3 mg, 0.313 mmol),THF (2 mL), and isocyanatobenzene (0.33 mL, 0.313 mmol). The resultingmixture was then agitated on an orbital shaker for 4.5 h at which timeit was concentrated to dryness in vacuo. The dried material was thenpurified by normal phase chromatography (gradient, EtOAc/Hexane) toprovide5-fluoro-4-(2-fluorobenzylamino)-2-oxo-N-phenylpyrimidine-1(2H)-carboxamide(75.3 mg, 68%) as a white solid: mp 154-157° C.; ¹H NMR (400 MHz, CDCl₃)δ 12.65 (s, 1H), 8.51 (d, J=7.1 Hz, 1H), 7.63-7.55 (m, 2H), 7.46 (td,J=7.5, 1.7 Hz, 1H), 7.41-7.28 (m, 3H), 7.19-7.05 (m, 3H), 6.03 (s, 1H),4.86 (d, J=5.9 Hz, 2H); ESIMS m/z 355 ([M−H]⁻).

Compounds 29-32 were prepared as in Example 7.

Example 8 Preparation of(E)-4-((dimethylamino)methyleneamino)-N,N-diethyl-5-fluoro-2-oxopyrimidine-1(2H)-carbothioamide(33)

A 25 mL screw-top vial was charged with(E)-N′-(5-fluoro-2-hydroxypyrimidin-4-yl)-N,N-dimethylformimidamide(99.7 mg, 0.541 mmol), CH₃CN (5 mL) and BSA (0.0665 mL, 0.272 mmol). Theresulting mixture was then agitated on a rotary shaker at 80° C. for 19h. After cooling to room temperature, thiophosgene (0.0415 mL, 0.544mmol) was added, and the reaction mixture was agitated at roomtemperature on a rotary shaker for 90 min. At this time, diethylamine(0.112 mL, 1.08 mmol) was added, and the reaction mixture was furtheragitated at room temperature for 1 h. The heterogenous mixture waspoured into a fritted funnel, and the resulting filtrate wasconcentrated in vacuo. This crude material was then purified by normalphase chromatography (gradient, 0 to 100% EtOAc/Hexane) to afford(E)-4-((dimethylamino)methyleneamino)-N,N-diethyl-5-fluoro-2-oxopyrimidine-1(2H)-carbothioamide(25.9 mg, 16%) as a pale yellow solid: mp 118-123° C.; ¹H NMR (400 MHz,DMSO-d₆) δ 8.60 (s, 1H), 8.41 (d, J=3.2 Hz, 1H), 3.20 (s, 3H), 3.34 (q,J=6.7 Hz, 4H), 3.09 (s, 3H), 1.17 (s, 3H), 1.08 (s, 3H); ESIMS m/z 300([M+H]⁺).

Example 9 Preparation of4-amino-5-fluoro-N-methyl-2-oxo-N-phenylpyrimidine-1(2H)-carbothioamide(34)

A 25 mL screw-top vial was charged with 4-amino-5-fluoropyrimidin-2-ol(100.1 mg, 0.775 mmol), CH₃CN (3 mL) and BSA (0.284 mL, 1.162 mmol). Theresulting mixture was then agitated on a rotary shaker at 65° C. for 90min. After cooling to room temperature, methyl(phenyl)carbamothioicchloride (157.6 mg, 0.849 mmol) was added, and the reaction mixture wasagitated on a rotary shaker at 65° C. for 16 h. After cooling to roomtemperature, the reaction mixture was diluted with CH₂Cl₂ (100 mL) andwashed with satd aq NaCl solution (50 mL×2). The organic layer was thendried over Na₂SO₄, filtered, and concentrated in vacuo to afford a greenoil. This crude material was then purified by normal phasechromatography (gradient, 0 to 35% MeOH/CH₂Cl₂) to provide4-amino-5-fluoro-N-methyl-2-oxo-N-phenylpyrimidine-1(2H)-carbothioamide(80.1 mg, 37%) as a 90% pure beige/green solid: mp 192-196° C.; ¹H NMR(400 MHz, DMSO-d₆) δ 8.16 (d, J=6.7 Hz, 1H), 7.83 (s, 1H), 7.66 (s, 1H),7.38 (m, 2H), 7.34-7.26 (m, 3H), 3.71 (s, 3H); ESIMS m/z 279 ([M+H]⁺).

Compounds 35-37 were prepared as in Example 9.

Example 10 Preparation of4-acetamido-N-ethyl-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide (38)

To a suspension of N-(5-fluoro-2-hydroxypyrimidin-4-yl)acetamide (asprepared in U.S. Pat. No. 3,309,359; 0.25 g, 1.46 mmol) in dry THF (5mL) was added ethyl isocyanate (0.127 mL, 1.61 mmol), and the mixturewas stirred at room temperature for 1 h. The solvent was removed invacuo, and the solid residue was suspended in Et₂O (10 mL). Thesuspension was suction filtered and washed with Et₂O (2×10 mL). Theresulting solid was dried in vacuo to yield4-acetamido-N-ethyl-5-fluoro-2-oxopyrimidine-1(2H)-carboxamide (0.350 g,99%) as a white solid: mp 233-235° C.; ¹H NMR (300 MHz, DMSO-d₆) δ 10.89(s, 1H), 10.01 (s, 1H), 8.62 (d, J=7.0 Hz, 1H), 3.40-3.27 (m, 2H), 2.30(s, 3H), 1.15 (t, J=7.2 Hz, 3H); ESIMS m/z 241

([M−H]⁻).

Compounds 39-48 were prepared as in Example 10.

Example 11 Preparation ofN-ethyl-5-fluoro-4-(3-(2-methoxybenzyl)ureido)-2-oxopyrimidine-1(2H)-carboxamide(49)

To a suspension of1-(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)-3-(2-methoxybenzyl)urea (asprepared in U.S. Patent Appl. Publ. 2010022538; 0.25 g, 0.855 mmol) indry THF (5 mL) was added ethyl isocyanate (0.074 mL, 0.941 mmol), andthe mixture was stirred at room temperature for 3 h. The solvent wasremoved in vacuo, and the solid residue was suspended in Et₂O (10 mL).The suspension was suction filtered and washed with Et₂O (2×10 mL). Theresulting solid was dried in vacuo to yieldN-ethyl-5-fluoro-4-(3-(2-methoxybenzyl)ureido)-2-oxopyrimidine-1(2H)-carboxamide(0.150 g, 48%) as a white solid: mp 248-250° C.; ¹H NMR (300 MHz,DMSO-d₆) δ 10.56 (s, 1H), 9.92 (s, 1H), 9.68 (s, 1H), 8.55 (d, J=6.6 Hz,1H), 7.33-7.20 (m, 2H), 7.02 (d, J=7.9 Hz, 1H), 6.91 (dd, J=7.9, 6.9 Hz,1H), 4.41 (d, J=6.0 Hz, 2H), 3.88 (s, 3H), 3.38-3.24 (m, 2H), 1.14 (t,J=7.2 Hz, 3H). ESIMS m/z 362 ([M−H]⁻).

Compounds 50-53 were prepared as in Example 11.

TABLE I Compounds and Related Characterization Data Appear- mp CmpdStructure ance MS (° C.) ¹H NMR (δ, DMSO-d₆) 2

white solid ESIMS m/z 328 ([M + H]⁺) 232- 236 10.42 (t, J = 5.9 Hz, 1H),8.77 (s, 1H), 8.36 (d, J = 6.9 Hz, 1H), 4.06 (q, J = 7.1 Hz, 2H), 3.51(q, J = 6.3 Hz, 2H), 3.28 (s, 3H), 3.15 (s, 3H), 2.58 (q, J = 6.5 Hz,2H), 1.17 (t, J = 7.1 Hz, 3H) 7

white solid ESIMS⁻ 276.94 277- 280 dec 12.93 (s, 1H), 8.59 (s, 1H), 8.44(d, J =7.58 Hz, 1H), 8.30 (s, 1H), 8.14-8.12 (m, 1H), 7.10- 7.06 (m,2H), 6.98-6.93 (m, 1H) 3.85 (s, 3H) 8

white solid ESIMS⁻ 281.1  258- 261 13.32 (s, 1H), 8.70 (s, 1H), 8.44 (d,J = 7.25 Hz, 1H), 8.39 (s, 1H), 8.23 (dd, J = 8.24, 1.65 Hz, 1H), 7.53(dd, J = 8.24, 1.32 Hz, 1H), 7.40-7.35 (m, 1H), 7.18-7.13 (m, 1H) 9

white solid ESIMS⁻ 261.2  277- 280 dec 12.76 (s, 1H), 8.65 (s, 1H), 8.45(d, J = 7.25 Hz, 1H), 8.35 (s, 1H), 7.96 (d, J = 7.58 Hz, 1H), 7.26-7.17(m, 2H) 7.08-7.03 (m, 1H) 2.26 (s, 3H) 10

white solid ESIMS⁻ 277.2  252- 255 12.65 (s, 1H), 8.62 (s, 1H), 8.44 (d,J = 7.42 Hz, 1H), 8.34 (s, 1H), 7.49-7.46 (m, 2H), 6.96- 6.93 (m, 2H),3.74 (s, 3H) 11

white solid ESIMS⁻ 298.86 251- 254 12.91 (s, 1H), 8.70 (s, 1H),8.50-8.34 (m, 2H), 7.91 (dd, J = 6.7, 2.6 Hz, 1H), 7.57-7.48 (m, 1H),7.44 (t, J = 9.0 Hz, 1H) 12

white solid ESIMS⁻ 282.8  261- 264 12.90 (s, 1H), 8.68 (s, 1H), 8.44 (d,J = 7.42 Hz, 1H), 8.39 (s, 1H), 7.62-7.59 (m, 2H), 7.45- 7.42 (m, 2H) 13

white solid ESIMS⁻ 272.1  254- 257 13.20 (s, 1H), 8.74 (s, 1H),8.47-8.43 (m, 2H), 7.86 (d, J = 8.7 Hz, 2H), 7.77 (d, J = 8.7 Hz, 2H) 15

white solid ESIMS⁻ 260.99 257- 260 12.73 (s, 1H), 8.62 (s, 1H), 8.43 (d,J = 7.4 Hz, 1H), 8.34 (s, 1H), 7.43 (d, J = 8.5 Hz, 2H), 7.17 (d, J =8.3 Hz, 2H), 2.27 (s, 3H) 16

white solid ESIMS⁻ 277.2  242- 244 12.83 (s, 1H), 8.65 (s, 1H), 8.43 (d,J = 7.4 Hz, 1H), 8.36 (s, 1H), 7.29-7.20 (m, 2H), 7.09- 7.04 (m, 1H),6.74-6.68 (m, 1H), 3.75 (s, 3H) 17

pale yellow solid ESIMS⁻ 296.9  273- 275 13.07 (s, 1H), 8.68 (s, 1H),8.50 (d, J = 7.4 Hz, 1H), 8.40 (s, 1H), 8.23 (d, J = 2.0 Hz, 1H),7.98-7.86 (m, 2H), 7.65-7.42 (m, 4H) 18

pale yellow solid ESIMS⁻ 299.99 268- 270 12.72 (s, 1H), 8.60 (s, 1H),8.48 (d, J = 7.4 Hz, 1H), 8.33 (s, 1H), 7.84 (d, J = 1.9 Hz, 1H), 7.44(d, J = 8.7 Hz, 1H), 7.35 (d, J = 3.0 Hz, 1H), 7.23 (dd, J = 8.7, 2.0Hz, 1H), 6.42 (d, J = 3.1 Hz, 1H), 3.79 (s, 3H) 19

white solid ESIMS⁻ 303.2  282- 284 12.96 (s, 1H), 8.66 (s, 1H), 8.49 (d,J = 7.4 Hz, 1H), 8.38 (s, 1H), 8.21 (d, J = 1.9 Hz, 1H), 8.00 (d, J =8.7 Hz, 1H), 7.81 (d, J = 5.5 Hz, 1H), 7.52-7.45 (m, 2H) 20

white solid ESIMS⁻ 253.2  263- 265 12.86 (s, 1H), 8.65 (s, 1H), 8.45 (d,J = 7.4 Hz, 1H), 8.37 (s, 1H), 7.59-7.53 (m, 2H), 7.23 (dd, J = 5.0, 1.6Hz, 1H) 21

white solid ESIMS⁻ 265.2  257- 259 12.81 (s, 1H), 8.67 (s, 1H), 8.45 (d,J = 7.4 Hz, 1H), 8.38 (s, 1H), 7.66-7.55 (m, 2H), 7.29- 7.19 (m, 2H) 22

white solid ESIMS m/z 279 ([M − H]⁻) 260- 262 10.71 (t, J = 5.6 Hz, 1H),8.5 (s, 1H), 8.34 (d, J = 7.2 Hz, 1H), 8.24 (s, 1H), 7.41-7.32 (m, 2H),7.23-7.17 (m, 2H), 4.53 (d, J = 5.6 Hz, 2H) 23

white solid ESIMS m/z 215 ([M + H]⁺) 290- 293 10.31 (t, J = 5.7 Hz, 1H),8.44 (s, 1H), 8.34 (d, J = 7.4 Hz, 1H), 8.19 (s, 1H), 3.26-3.19 (m, 2H),1.57-1.48 (m, 2H), 0.88 (t, J = 7.0 Hz, 3H) 24

white solid ESIMS m/z 215 ([M + H]⁺) 291- 294 10.28 (d, J = 7.2 Hz, 1H),8.46 (s, 1H), 8.34 (d, J = 7.4 Hz, 1H), 8.20 (s, 1H), 3.88 (dq, J =13.3, 6.6 Hz, 1H), 1.18 (d, J = 6.6 Hz, 6H). 25

white solid ESIMS m/z 257 ([M − H]⁻) 220- 224 10.53 (t, J = 5.7 Hz, 1H),8.50 (s, 1H), 8.33 (d, J = 7.4 Hz, 1H), 8.27 (s, 1H), 4.17-4.05 (m, 4H),1.20 (t, J = 7.1 Hz, 3H) 26

pale pink solid ESIMS m/z 245 ([M − H]⁻) 237- 239 10.43 (t, J = 5.6 Hz,1H), 8.46 (s, 1H), 8.35 (d, J = 7.5 Hz, 1H), 8.21 (s, 1H), 3.53-3.42 (m,2H), 2.64 (t, J = 6.7 Hz, 2H), 2.08 (s, 3H) 27

white solid ESIMS m/z 243 ([M − H]⁻) 295- 298 10.31 (t, J = 5.5 Hz, 1H),8.44 (s, 1H), 8.34 (d, J = 7.5 Hz, 1H), 8.19 (s, 1H), 3.41-3.26 (m, 4H),3.23 (s, 3H), 1.74 (p, J = 6.5 Hz, 2H) 29

white solid ESIMS m/z 391 ([M − H]⁻) 150- 153 (300 MHz, CDCl₃) 12.86 (s,1H), 8.46 (d, J = 7.1 Hz, 1H), 8.18-8.03 (m, 1H), 7.47 (t, J = 7.3 Hz,1H), 7.34 (dd, J = 13.9, 6.7 Hz, 1H), 7.23-7.05 (m, 2H), 6.99-6.84 (m,2H), 6.11 (s, 1H), 4.86 (d, J = 5.9 Hz, 2H) 30

white solid ESIMS m/z 369 ([M − H]⁻) 158- 162 (300 MHz, CDCl₃) 12.55 (s,1H), 8.51 (d, J = 7.2 Hz, 1H), 7.46 (d, J = 8.2 Hz, 3H), 7.34 (dd, J =13.4, 6.2 Hz, 1H), 7.21- 7.05 (m, 4H), 6.05 (s, 1H), 4.86 (d, J = 5.8Hz, 2H), 2.34 (s, 3H) 31

white solid ESIMS m/z 389 ([M − H]⁻) 158- 160 (300 MHz, CDCl₃) 12.78 (s,1H), 8.47 (d, J = 7.1 Hz, 1H), 7.73 (s, 1H), 7.51-7.23 (m, 4H),7.21-7.06 (m, 3H), 6.11 (s, 1H), 4.86 (d, J = 5.8 Hz, 2H) 32

white solid ESIMS m/z 321 ([M − H]⁻) 113- 116 (300 MHz, CDCl₃) 10.31 (s,1H), 8.42 (d, J = 12 Hz, 1H), 7.43 (t, J = 7.4 Hz, 1H), 7.32 (dd, J =14.0, 6.7 Hz, 1H), 7.18- 7.02 (m, 2H), 6.02 (s, 1H), 4.82 (d, J = 5.8Hz, 2H), 3.34 (dd, J = 13.0, 6.7 Hz, 2H), 1.72-1.56 (m, 2H), 0.97 (t, J= 7.4 Hz, 3H) 35

yellow solid ESIMS m/z 347 ([M + H]⁺) 126- 131 8.20 (d, J = 6.8 Hz, 1H),7.90 (s, 1H), 7.81-7.56 (m, 5H), 3.76 (s, 3H) 36

pale yellow solid ESIMS m/z 347 ([M + H]⁺) 200- 203 8.16 (d, J = 6.7 Hz,1H), 7.99 (s, 1H), 7.84 (s, 1H), 7.59 (s, 1H), 7.49 (d, J = 1.9 Hz, 2H),3.71 (s, 3H) 37

off- white solid ESIMS m/z 293 ([M + H]⁺) 223- 226 8.15 (d, J = 6.7 Hz,1H), 7.81 (s, 1H), 7.63 (s, 1H), 7.42-7.35 (m, 2H), 7.35-7.23 (m, 3H),4.37 (dq, J = 14.2, 7.1 Hz, 1H), 4.05 (dq, J = 14.2, 7.1 Hz, 1H), 1.20(t, J = 7.1 Hz, 3H) 39

white solid ESIMS m/z 255 ([M − H]⁻) 233- 235 (300 MHz, CDCl₃) 10.13 (s,1H), 8.65 (d, J = 6.6 Hz, 1H), 8.38 (s, 1H), 3.39 (td, J = 7.0, 5.8 Hz,2H), 2.68 (s, 3H), 1.75- 1.52 (m, 2H), 0.99 (t, J = 7.4 Hz, 3H) 40

white solid ESIMS m/z 317 ([M − H]⁻) 258- 260 11.98 (s, 1H), 9.49 (s,1H), 8.48 (s, 1H), 8.01-7.88 (m, 2H), 7.59 (m, 3H), 3.33-3.21 (m, 2H),1.75-1.33 (m, 2H), 0.90 (t, J = 7.4 Hz, 3H) 41

white solid ESIMS m/z 283 ([M − H]⁻) 226- 228 10.82 (s, 1H), 10.05 (s,1H), 8.6 (d, J = 5.1 Hz, 1H), 3.28-3.21 (m, 2H), 3.0-2.85 (m, 1H),1.58-1.46 (m, 2H), 1.07 (d, J = 6.86 Hz, 6H), 0.89 (t, J = 7.14 Hz, 3H)42

white solid ESIMS m/z 351 ([M − H]⁻) 239- 241 11.74 (s, 1H), 9.95 (s,1H), 8.65 (s, 1H), 7.69-7.42 (m, 4H), 3.34-3.21 (m, 2H), 1.63-1.45 (m,2H), 0.89 (t, J = 7.14 Hz, 3H) 43

light yellow solid ESIMS m/z 361 ([M − H]⁻) 227- 229 11.06 (s, 1H),10.05 (s, 1H), 8.63 (d, J = 7.3 Hz, 1H), 7.28- 7.17 (m, 2H), 6.95-6.84(m, 2H), 3.87 (s, 2H), 3.73 (s, 3H), 3.33-3.13 (m, 2H), 1.64-1.45 (m,2H), 0.89 (t, J = 7.14 Hz, 3H) 44

white solid ESIMS m/z 303 ([M − H]⁻) 249- 251 11.97 (s, 1H), 9.21 (s,1H), 8.55-8.25 (m, 1H), 8.04-7.89 (m, 2H), 7.71-7.46 (m, 3H), 3.36-3.28(m, 2H), 1.14 (t, J = 12 Hz, 3H) 45

white solid ESIMS m/z 269 ([M − H]⁻) 226- 228 10.88 (s, 1H), 10.02 (s,1H), 8.61 (d, J = 7.0 Hz, 1H), 3.37- 3.28 (m, 2H), 3.05-2.87 (m, 1H),1.27-1.03 (m, 9H) 46

pale brown solid ESIMS m/z 337 ([M − H]⁻) 239- 241 11.74 (s, 1H), 9.84(s, 1H), 8.64 (s, 1H), 7.58-7.40 (m, 4H), 3.43-3.18 (m, 2H), 1.18-1.10(t, J = 7.42 Hz, 3H) 47

white solid ESIMS m/z 337 ([M − H]⁻) 170- 172 10.91 (s, 1H), 10.44 (s,1H), 8.61 (d, J = 7.0 Hz, 1H), 7.56- 7.25 (m, 4H), 4.52 (d, J = 6.0 Hz,2H), 2.31 (s, 3H) 48

white solid ESIMS m/z 399 ([M − H]⁻) 210- 212 (300 MHz, CDCl₃) 12.99 (s,1H), 9.58 (s, 1H), 8.55 (d, J = 6.6 Hz, 1H), 8.31 (d, J = 6.6 Hz, 2H),7.67-7.57 (m, 1H), 7.54-7.45 (m, 2H), 7.39-7.24 (m, 4H), 4.57 (d, J =5.8 Hz, 2H) 50

white solid ESIMS m/z 376 ([M − H]⁻) 251- 253 10.58 (s, 1H), 9.91 (d, J= 7.3 Hz, 1H), 9.66 (s, 1H), 8.55 (d, J = 7.1 Hz, 1H), 7.35-7.19 (m,2H), 7.02 (d, J = 8.1 Hz, 1H), 6.92 (t, J = 7.3 Hz, 1H), 4.41 (d, J =5.3 Hz, 2H), 3.97-3.85 (m, 4H), 1.20 (d, J = 6.6 Hz, 6H) 51

white solid ESIMS m/z 376 ([M − H]⁻) 248- 250 10.57 (s, 1H), 9.98 (s,1H), 9.68 (s, 1H), 8.55 (d, J = 6.7 Hz, 1H), 7.33-7.21 (m, 2H), 7.02 (d,J = 7.9 Hz, 1H), 6.91 (td, J = 7.4, 0.9 Hz, 1H), 4.41 (d, J = 5.9 Hz,2H), 3.88 (s, 3H), 3.32- 3.20 (m, 2H), 1.62-1.45 (m, 2H), 0.89 (t, J =7.4 Hz, 3H) 52

white solid ESIMS m/z 404 ([M − H]⁻) 248- 250 10.57 (s, 1H), 9.97 (s,1H), 9.67 (s, 1H), 8.55 (d, J = 6.4 Hz, 1H), 7.33-7.21 (m, 2H), 7.02 (d,J = 8.2 Hz, 1H), 6.91 (td, J = 7.5, 0.9 Hz, 1H), 4.41 (d, J = 5.6 Hz,2H), 3.87 (s, 3H), 3.35- 3.22 (m, 2H), 1.59-1.45 (m, 2H), 1.36-1.21 (m,4H), 0.87 (t, J = 6.9 Hz, 3H) 53

white solid ESIMS m/z 442 ([M − H]⁻) 229- 231 10.59 (s, 1H), 10.38 (s,1H), 9.67 (s, 1H), 8.55 (d, J = 7.0 Hz, 1H), 7.48-7.13 (m, 6H), 7.02 (d,J = 7.9 Hz, 1H), 6.91 (td, J = 7.4, 0.9 Hz, 1H), 4.57 (d, J = 5.9 Hz,2H), 4.41 (d, J = 5.4 Hz, 2H), 3.87 (s, 3H) 1All spectra were recordedin DMSO-d₆ at 300 or 400 MHz unless otherwise stated.

Example 7 Evaluation of Fungicidal Activity: Leaf Blotch of Wheat(Mycosphaerella graminicola; Anamorph: Septoria tritici; Bayer CodeSEPTTR)

Wheat plants (variety Yuma) were grown from seed in a greenhouse in 50%mineral soil/50% soil-less Metro mix until the first leaf was fullyemerged, with 7-10 seedlings per pot. These plants were inoculated withan aqueous spore suspension of Septoria tritici either prior to or afterfungicide treatments. After inoculation the plants were kept in 100%relative humidity (one day in a dark dew chamber followed by two tothree days in a lighted dew chamber) to permit spores to germinate andinfect the leaf. The plants were then transferred to a greenhouse fordisease to develop.

The following table presents the activity of typical compounds of thepresent disclosure when evaluated in these experiments. Theeffectiveness of the test compounds in controlling disease wasdetermined by assessing the severity of disease on treated plants, thenconverting the severity to percent control based on the level of diseaseon untreated, inoculated plants.

-   -   In each case of Table II the rating scale is as follows:

% Disease Control Rating  76-100 A 51-75 B 26-50 C  0-25 D Not Tested E

TABLE II One-Day Protectant (1DP) and Three-Day Curative (3DC) Activityof Compounds on SEPTTR at 100 ppm SEPTTR SEPTTR 100 PPM 100 PPM Cmpd 1DP3DC 1 A A 2 A A 3 A A 4 A A 5 A A 6 A A 7 A A 8 A A 9 A A 10 A A 11 A C12 A A 13 A B 14 A A 15 A A 16 A A 17 A A 18 A A 19 A A 20 A A 21 A A 22A A 23 A A 24 A A 25 A A 26 A A 27 A A 28 D C 29 D C 30 D C 31 D D 32 CB 33 D C 34 A A 35 A A 36 A A 37 A A 38 A A 39 A A 40 A A 41 A A 42 C A43 A A 44 A A 45 A A 46 A B 47 A A 48 A A 49 D D 50 D D 51 D D 52 D D 53D D

What is claimed is:
 1. A compound of Formula I:

wherein R¹ is: H; C₁-C₆ alkyl optionally substituted with 1-3 R⁴; C₂-C₆alkenyl optionally substituted with 1-3 R⁴; C₃-C₆ alkynyl optionallysubstituted with 1-3 R⁴; phenyl, or benzyl wherein each of the phenyl orthe benzyl may be optionally substituted with 1-3 R⁵, or with a 5- or6-membered saturated or unsaturated ring system, or with a 5-6 fusedring system, or with a 6-6 fused ring system each containing 1-3heteroatoms wherein each ring may be optionally substituted with 1-3 R⁵,biphenyl or naphthyl optionally substituted with 1-3 R⁵; —(CHR⁶)_(m)OR⁷;—C(═O)R⁸; —C(═S)R⁸; —C(═O)OR⁸; —C(═S)OR⁸; —(CHR⁶)_(m) N(R⁹)R¹⁰;—C(═O)N(R⁹)R¹⁰; or —C(═S)N(R⁹)R¹⁰; wherein m is an integer 1-3; R² is Hor C₁-C₆ alkyl optionally substituted with R⁴; alternatively R¹ and R²may be taken together to form ═CR¹¹N(R¹²)R¹³; R³ is —C(═O)N(R⁹)R¹⁰ or—C(═S)N(R⁹)R¹⁰; R⁴ is independently halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄haloalkylthio, halothio, amino, C₁-C₃ alkylamino, C₂-C₆ alkoxycarbonyl,C₂-C₆ alkylcarbonyl, C₂-C₆ alkylaminocarbonyl, hydroxyl, or C₃-C₆trialkylsilyl; R⁵ is independently halogen, C₁-C₆ alkyl, C₁-C₆haloalkyl, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆haloalkylthio, halothio, amino, C₁-C₆ alkylamino, C₂-C₆ dialkylamino,C₂-C₆ alkoxycarbonyl, or C₂-C₆ alkylcarbonyl, nitro, hydroxyl, or cyano;R⁶ is H, C₁-C₆ alkyl, C₁-C₆ alkoxy, benzyl or phenyl wherein each of thebenzyl or phenyl may be optionally substituted with 1-3 R⁵; R⁷ is H,C₁-C₆ alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆alkoxyalkyl, C₂-C₆ alkylcarbonyl, phenyl, or benzyl wherein each of thephenyl, or the benzyl may be optionally substituted with 1-3 R⁵, or witha 5- or 6-membered saturated or unsaturated ring system, or with a 5-6fused ring system, or with a 6-6 fused ring system each containing 1-3heteroatoms wherein each ring may be optionally substituted with 1-3 R⁵,biphenyl or naphthyl optionally substituted with 1-3 R⁵; R⁸ is H, C₁-C₆alkyl, C₂-C₆ alkenyl, C₃-C₆ alkynyl, C₁-C₆ haloalkyl, C₁-C₆ alkoxyalkyl,phenyl or benzyl wherein each of the phenyl or the benzyl may beoptionally substituted with 1-3 R⁵, or with a 5- or 6-membered saturatedor unsaturated ring system, or with a 5-6 fused ring system, or with a6-6 fused ring system each containing 1-3 heteroatoms wherein each ringmay be optionally substituted with 1-3 R⁵, biphenyl or naphthyloptionally substituted with 1-3 R⁵; R⁹ is H, C₁-C₆ haloalkyl, C₁-C₆alkoxyalkyl, C₁-C₆ alkylalkoxycarbonyl, C₂-C₆ alkylcarbonyl,—(CH₂)_(m)SCH₃, phenyl or benzyl wherein each of the phenyl or thebenzyl may be optionally substituted with 1-3 R⁵, or with a 5- or6-membered saturated or unsaturated ring system, or with a 5-6 fusedring system, or with a 6-6 fused ring system each containing 1-3heteroatoms wherein each ring may be optionally substituted with 1-3 R⁵,biphenyl or naphthyl optionally substituted with 1-3 R⁵; R¹⁰ is H, C₁-C₆haloalkyl, C₁-C₆ alkoxyalkyl, C₂-C₆ alkylcarbonyl, or benzyl, whereinthe benzyl may be optionally substituted with 1-3 R⁵; alternatively R⁹and R¹⁰ may be taken together to form a 5- or 6-membered saturated orunsaturated ring containing 1-3 heteroatoms wherein each ring may beoptionally substituted with 1-3 R⁵; R¹¹ is H or C₁-C₄ alkyl; R¹² is H,cyano, hydroxyl, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆, alkylcarbonyl, phenylor benzyl wherein each of the phenyl or the benzyl may be optionallysubstituted with 1-3 R⁵; or with a 5- or 6-membered saturated orunsaturated ring system, or with a 5-6 fused ring system, or with a 6-6fused ring system each containing 1-3 heteroatoms wherein each ring maybe optionally substituted with 1-3 R⁵, biphenyl or naphthyl optionallysubstituted with 1-3 R⁵; alternatively R¹¹ and R¹² may be taken togetherto form a 5- or 6-membered saturated or unsaturated ring containing 1-3heteroatoms wherein each ring may be optionally substituted with 1-3 R⁵;R¹³ is H, C₁-C₄ alkyl, C₁-C₆ alkoxy, C₂-C₆, alkylcarbonyl, phenyl orbenzyl wherein each of the phenyl or the benzyl may be optionallysubstituted with 1-3 R⁵; and alternatively R¹² and R¹³ may be takentogether to form a 5- or 6-membered saturated or unsaturated ringcontaining 1-3 heteroatoms wherein each ring may be optionallysubstituted with 1-3 R⁵.
 2. The compound according to claim 1, whereinR¹ is H; and R² is H.
 3. The compound according to claim 2, wherein R³is —C(═O)N(R⁹)R¹⁰; and R¹⁰ is H.
 4. The compound according to claim 3,wherein R⁹ is phenyl or benzyl wherein each of the phenyl or the benzylmay be optionally substituted with 1-3 R⁵, a 5- or 6-membered saturatedor unsaturated ring system optionally substituted with 1-3 R⁵, a 5-6fused ring system, or a 6-6 fused ring system each containing 1-3heteroatoms wherein each ring may be optionally substituted with 1-3 R⁵,or biphenyl or naphthyl optionally substituted with 1-3 R⁵.
 5. Thecompound according to claim 1, wherein the compound of formula I is:


6. The compound according to claim 1, wherein the compound of formula Iis:


7. The compound according to claim 1, wherein the compound of formula Iis:


8. The compound according to claim 1, wherein R⁹ is phenyl or benzylwherein each of the phenyl or the benzyl may be optionally substitutedwith 1-3 R⁵, a 5- or 6-membered saturated or unsaturated ring systemoptionally substituted with 1-3 R⁵, a 5-6 fused ring system or a 6-6fused ring system each containing 1-3 heteroatoms wherein each ring maybe optionally substituted with 1-3 R⁵, or biphenyl or naphthyloptionally substituted with 1-3 R⁵.
 9. The compound according to claim1, wherein R⁹ is a 5-6 fused ring system or a 6-6 fused ring system eachcontaining 1-3 heteroatoms wherein each ring may be optionallysubstituted with 1-3 R⁵.
 10. The compound according to claim 1, whereinR⁹ is biphenyl or naphthyl optionally substituted with 1-3 R⁵.
 11. Acomposition for the control of a fungal pathogen including the compoundof claim 1 and a phytologically acceptable carrier material.
 12. Thecomposition of claim 11 wherein the fungal pathogen is Apple Scab(Venturia inaequalis), Leaf Blotch of Wheat (Septoria tritici), LeafSpot of Sugarbeets (Cercospora beticola), Leaf Spots of Peanut(Cercospora arachidicola and Cercosporidium personatum), and BlackSigatoka of Banana (Mycosphaerella fijiensis).
 13. A method for thecontrol and prevention of fungal attack on a plant, the method includingthe steps of: applying a fungicidally effective amount of at least oneof the compounds of claim 1 to at least one of the plant, an areaadjacent to the plant, soil adapted to support growth of the plant, aroot of the plant, foliage of the plant, and a seed adapted to producethe plant.